Formaldehyde → 2-(2-Hydroxy-3-diethylaminomethyl-5-methylphenyl)-2H-benzotriazole

HRID 1756466Notes

Reaction equation

HRID 1756466 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]2=[N:10]1.[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19].C=O.[C:25]1(C)C=CC=CC=1>C(O)CCC>[OH:1][C:2]1[C:7]([CH2:25][N:20]([CH2:21][CH3:22])[CH2:18][CH3:19])=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]2=[N:10]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1140TolueneHCID 8021DiethylamineHCID 17113Drometrizole

Product 1

HCID 159190222-(2-Hydroxy-3-diethylaminomethyl-5-methylphenyl)-2H-benzotriazole

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
97.5 °C

Procedure

2-(2-Hydroxy-5-methylphenyl)-2H-benzotriazole (74.3 g, 0.33 mol), diethylamine (37.0 g, 0.51 mol) and paraformaldehyde (17.1 g) are dissolved in 85 mL of n-butanol. The mixture is heated with agitation at reflux (95 to 100° C.) for 44 hours. The solvent is then removed by vacuum distillation to give a yellow viscous liquid as product in high yield (>99%). This Mannich base is identified as the above-named compound by thin layer chromatography using toluene as the mobile phase.

Workup

  1. temperatureThe mixture is heated with agitation
  2. customThe solvent is then removed by vacuum distillation
  3. customto give a yellow viscous liquid as product
  4. customin high yield (>99%)

Sources & evidence

ORD record
ord-93709aa5ea384852ba00adfd7d9f6ddd
Source dataset
uspto-grants-1995_08
Patent number
US05439955

Reaction notes

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